‘Mr. Key West,’ who made the island into a destination, dies

In 1962, Key West, Fla., was a remote naval outpost on six square miles of limestone rock, mostly notable for its proximity to Cuba. Rickety wood-frame houses lined its streets, at times threatening to collapse. The declining waterfront, once a busy trading port, offered visitors little more than a selection of weather-beaten bars.

David Wolkowsky, who had returned to the city of his birth after years away, saw something else: potential. For the next few decades, he devoted himself to the task of restoring the island’s dilapidated historic buildings, eventually helping Key West become a resort destination that draws visitors from all over the world.

On Sunday, the Miami Herald reported that Wolkowsky had died at the age of 99.

Though tourists may not know the name of the man who became known as “Mr. Key West,” many locals credit him with transforming the island. “We often say whatever you like about Key West can be put on his doorstep because that’s really true,” Claude Reams, who owns a menswear store in Key West, told the Herald in 2012.

By salvaging turn-of-thecentury homes, Wolkowsky helped ensure the city retained a distinctive sense of character. Key West has an enduring eccentricity that prevents it from being just another seaside tourist town: Free-range roosters wander the streets with impunity, bougainvillea sprouts from yards with wild abandon, and a year-round crew of crusty burnouts provides a welcome contrast to the tourists lining up for fudge and trolley tours. Instead of high-rise condominiums, the city offers something rare in Florida: a sense of history.

“David began to renovate those buildings and really, I think, was one of the main people responsible for the historic preservation movement and for showing people that Key West’s past, its history was worth saving, had a certain glamour to it, was beautiful,” Arlo Haskell, a local historian, told Miami-based radio station WLRN this week.

Deeply embedded

Wolkowsky’s own family was deeply embedded in that history. His grandfather, Abraham, first arrived there in 1886 and quickly went from being a street peddler to becoming a successful local businessman, Haskell, who is also the author of “The Jews of Key West,” told WLRN. The family business eventually included clothing stores, saloons, a furniture store and billiards hall.

David Wolkowsky was born in Key West in 1919. Several years later, the city went through an economic slump after a devastating hurricane hit the island, and the Navy pulled out many of its operations in the wake of World War I.

“We left on the train when I was 4 and moved to Miami,” Wolkowsky told the Key West Citizen in 2016. “I can remember eating guava jelly on Saltine crackers in the dining car of the train.”

After finishing school in Miami, Wolkowsky enrolled at the University of Pennsylvania as a pre-med student. He soon realized he wasn’t cut out for medicine and switched his focus to architecture instead, he told Bitter Southerner magazine in a profile published this summer. After graduating and spending four years in the Merchant Marine, he eventually made his way back to Philadelphia, where he began renovating and rehabilitating shabby rowhouses in the city’s urban core.

“People all took trains out to apartments and houses on the main line then, and I coaxed them into living in Center City,” he recalled in the Bitter Southerner profile.

When Wolkowsky was 42, his father died and he inherited a handful of aging buildings in Key West. Initially, he had thought he would retire, he often told reporters in later years. But, instead, he made the radical and somewhat risky decision to buy more underappreciated pieces of property in Key West, including a former cigar factory, a bar where Ernest Hemingway used to drink and an old dime store.

His efforts to preserve and protect ramshackle old buildings went against the conventional wisdom of the 1960s. Throughout the country, cities were bulldozing blighted historic neighborhoods in the name of urban renewal. Walkable, tightly packed commercial strips like Key West’s Duval Street were falling out of favor, and quickly being replaced by shopping centers with ample parking.

Wolkowsky instead chose to invest in Key West’s historic Old Town. In 1968, he opened the Pier House, a waterfront hotel which “quickly earned a reputation for being as quirky and unpredictable as Wolkowsky himself,” Islands Magazine wrote in a 1993 profile.

‘Turning point’

Jimmy Buffett played some of his first gigs at the bar, and Wolkowsky invited literary celebrities like Tennessee Williams and Truman Capote, both of whom became good friends, to come and stay. Many years later, the Miami Herald identified the opening of the Pier House as “the turning point in Key West’s transformation from washed-up military outpost to funky tourist destination.”

It didn’t take long before other developers followed. By 1980, the Miami News reported that Key West had “evolved from a languid little island backwater [ ...] to America’s quintessential resort for urban sophisticates.”

Typically dressed in Panama hats and crisp white linen button-down shirts, Wolkowsky rode around Key West in golf carts and a vintage RollsRoyce. Up until his death, he also owned the southernmost private home in the contiguous United States, where he famously served potato chips and turkey dogs to his prominent guests.

In 1974, he purchased Ballast Key, a small rocky island located roughly eight miles from Key West, for $160,000. “I used to come out and picnic here when it was a deserted island,” he told the South Florida Sun-Sentinel’s Sunshine magazine in 1983. “And I’d see people cutting down these mangrove trees which took decades to grow, cutting them to make hot dog fires and I’d get annoyed. Then I got interested in buying the island to protect it.”

Building a stilt home on the island “took years and required both a barge and a desalinization plant,” the Miami Herald reported. In August, the Monroe County Commission voted to rename the island “David Wolkowsky Key.” The name change has not been made official, since the U.S. Board of Geographic Names doesn’t consider applications until five years after a person has died.

On Aug. 25, Mr. Key West celebrated his 99th birthday “in true Wolkowsky style,” the Miami Herald reported. There were orchids, champagne and gifts of pearl necklaces for each of the women who attended. He died at the Lower Keys Medical Center in Key West nearly a month later, on Sept. 23.